South Chicago Vacations from ￥662,926

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The Latest South Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥1,007,204, price is now ￥662,926 per person
￥662,926
per person
Aug 13 - Aug 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,256 reviews)
The Silversmith Hotel in Chicago offers a fantastic stay with its prime downtown location, just steps from Millennium Park and the Art Institute. The rooms are a blend of modern comfort and historic charm, featuring high ceilings, large windows, and plush beds for a restful night. Guests consistently praise the friendly, attentive staff who provide excellent service, including helpful recommendations for local attractions and dining. While there’s no on-site restaurant, a delightful bar and breakfast is available in the lobby, and numerous dining options are within walking distance. Overall, the Silversmith Hotel provides great value and a memorable experience for both business and leisure travelers.

Reviewed on Jul 2, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥1,032,808, price is now ￥670,259 per person
￥670,259
per person
Aug 13 - Aug 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay.

Reviewed on Jul 2, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥1,111,172, price is now ￥727,868 per person
￥727,868
per person
Aug 13 - Aug 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Excellente

Reviewed on Jul 1, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥1,058,930, price is now ￥697,630 per person
￥697,630
per person
Aug 13 - Aug 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
10/10

Reviewed on Jul 3, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥1,026,532, price is now ￥677,551 per person
￥677,551
per person
Aug 13 - Aug 20
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,141 reviews)
The location of the Arlo Chicago is super convenient and the hotel is quiet and comfy.

Reviewed on Jul 2, 2026

Where to stay in South Chicago

Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

South Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥19,584 per night from Jul 6 to Jul 7
￥19,584
￥23,283 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very Good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on Jul 2, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,642 per night from Jul 5 to Jul 6
￥24,642
￥34,666 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,834 reviews)
"We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay."

Reviewed on Jul 2, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥32,091 per night from Jul 5 to Jul 6
￥32,091
￥38,154 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (4,483 reviews)
"A lot of it was good, the rooms were very good. The AC was very good and the view from the bedroom. The only things I want to complain about is the expensive stuff and the TV in the bedroom not working/turning on. It costs a lot of money for car parking. The beds were one of the most comfortable ..."

Reviewed on Jul 3, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,195 properties in South Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a South Chicago vacation package cost?
Live it up in South Chicago from just ￥662,926. Choose from a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your vacation package.
How do I get a cheap travel package to South Chicago?
Combine your flights and hotels, toss in extras such as activities or a rental car, and save with a South Chicago vacation package. You won't just pick up impressive discounts on your escape — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels around the globe. Your dream vacation starts right here, right now!
Where should I stay in South Chicago?
With so much to do in South Chicago, it's a good idea to secure a room in a hotel close to its attractions. Calumet Beach, Calumet Park and Bronzeville Childrens Museum are some interesting ones to put on your must-see list.
How far in advance should I book my South Chicago vacation?
While not all airlines release ticket prices early, it's usually possible to compare international fares on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you're purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks before departure.
What does an Expedia South Chicago travel package include?
From hotels and flights to car rentals, Expedia can help you craft a South Chicago package that fits you. Heading away for a week or longer? Consider a flight, rental car and hotel bundle. If you're taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added after you've booked. Our packages make it a cinch to plan and save.
What should I know before booking a South Chicago travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fantastic discounts. You're not restricted to hotels, though. We've got island resorts, cozy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia vacation package?
Yes, of course. Expedia has access to more than 550 airline partners around the world, so fly with the carrier that best fits your budget and traveling style.
If I'm not able to travel, can I cancel my South Chicago vacation package?
If your vacation plans in South Chicago have changed, it's good to know that it's possible to cancel your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.

Stay near popular South Chicago attractions

Mahalia Jackson Residence

You can find out about the history of Chicago with a visit to Mahalia Jackson Residence. Experience the area's entertainment venues and live music.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,887
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,398
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.